Sodium hydride → 5-Cyclohexyl-1-[2-[4-(phenylmethyl)-1-piperazinyl]ethyl]-1H-indole-2,3-dione

HRID 1081268Notes

Reaction equation

HRID 1081268 reaction equation
[CH:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]3=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:25][CH2:24]1>CN(C=O)C>[CH:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:25][CH2:24]2)[C:11](=[O:16])[C:10]3=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 47416341-Benzyl-4-(2-chloroethyl)piperazineHCID 125119305-Cyclohexylindoline-2,3-dione

Product 1

HCID 99106275-Cyclohexyl-1-[2-[4-(phenylmethyl)-1-piperazinyl]ethyl]-1H-indole-2,3-dioneYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-Cyclohexyl-1H-indole-2,3-dione (3.45 g) in dry DMF at 0° C. was treated with sodium hydride (80% dispersion in mineral oil, 550 mg). The mixture was allowed to warm to room temperature and 1-(2-chloroethyl)-4-(phenylmethyl) piperazine (3.9 g) in dry DMF (25 ml) was added. The reaction mixture was then heated in an oil bath at 70° C. for 2 hours. The mixture was evaporated under reduced pressure and the residue passed through a pad of silica gel to yield the title compound as a red oil (4.2 g, 65%).

Workup

  1. temperatureThe reaction mixture was then heated in an oil bath at 70° C. for 2 hours
  2. customThe mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0e0390f1e83f4def897318b0a949dba0
Source dataset
uspto-grants-1996_12
Patent number
US05585378

Reaction notes

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